Khyentse James's grandparents were radio performers during the 1940's. In a conversation with the Los Angeles Times, Khyentse said that the "warmth and nostalgia" of her grandparents' era really struck a chord with her, and that she sometimes felt as though she belonged to the wrong generation. Those time-swept feelings inspired Khyentse to throw the first World War II 1940's Era Ball, a spectacle complete with the same vehicles, props, and bald eagle bartenders used by The Greatest Generation.

The success of that initial event led her to host equally inspired celebrations just like it throughout the year. Today, the non-profit organization recognized as 1940's Ball produces three events annually, including a Hawaiian-themed tiki bash during the summer and and White Christmas gala in the winter. At each, the goal is to create connections throughout the community that cross generations with a festive lineup of food, décor, and, most importantly, live entertainment popularized during bygone eras.